The Most Hated Salesperson: A New Perspective with Benjamin Dennehy

Is your sales approach costing you deals? Are you too soft on prospects when you should be closing? In this episode, I sit down with Benjamin Dennehy—dubbed the UK’s Most Hated Salesperson—to strip away the fluff and expose what truly works in sales and recruitment. Love him or hate him, Benjamin’s approach is bold, direct, and brutally effective. We dive into Benjamin’s past and how he became the character he is today. He shares incredible insights into what to say in sales meetings, how to close, and strip away those prospects that aren’t right for you. His magic trick is getting the room when people don’t even know his name or what he does - and selling. If you’re in sales, recruitment, or business development, this episode will challenge everything you think you know about selling. Ready for a sales reality check? Tune in now! “I don't think you should be yourself in sales.” – Benjamin Dennehy You'll hear about: ✅ The psychology behind closing deals—why most people get it wrong ✅ Cold calling secrets that actually work (if you have the guts to use them) ✅ The art of questioning—how to control the conversation and qualify leads fast ✅ Recruitment sales tactics that separate amateurs from the pros ✅ Why personal branding and LinkedIn are game-changers in today’s market 00:00 - Identity and Role Separation 03:10 - Journey from Law to Sales 05:52 - Directness in Communication 09:02 - Sales Philosophy and Mindset 15:00 - The Art of Questioning in Sales 20:57 - The Most Hated Salesperson 24:00 - Recruitment as a Sales Role 32:59 - The Power of Live Call Calling 36:23 - Navigating LinkedIn: The Good, Bad, and Ugly 41:23 - The Role of Personal Branding in Sales 47:57 - Qualifying Leads: The Art of Disqualification 54:56 - Mastering the Conversation: The Key to Sales Success 01:00:45 - Mastering the Close 01:06:30 - The Psychology of Sales Conversations 01:16:48 - Balancing Personal and Professional Identity 01:19:19 - Leveraging LinkedIn for Success 01:21:29 - Avoiding Common Sales Pitfalls Benjamin’s resources: LinkedIn - https://www.linkedin.com/in/benjamindennehy/ YouTube - https://www.youtube.com/c/UKsMostHatedSalesTrainer UK’s most hated sales trainer - https://www.uksmosthatedsalestrainer.com/ Sales Matrix Courses - https://www.salesmatrixcourses.com/free/10-reasons-prospecting-course My resources: LinkedIn - https://www.linkedin.com/in/itschrisoconnell/ Twitter - https://twitter.com/ChrisOConnell11 Instagram - https://www.instagram.com/chrisoconnellcoach/ TikTok - https://www.instagram.com/chrisoconnellcoach/ YouTube - https://www.youtube.com/channel/UC_ZWYrxrzzaElmpZMy5S86w Basemindset website - https://basemindset.com/ Pre-order my new book - https://access.basemindset.com/pre-order